San Mateo is fortunate to retain the character and history of its growth from small town to prominent city in its architecture. On B Street and Third Avenue especially a majority of original structures still line San Mateo’s streets.

The ground floors of many of the buildings have been altered through the years. To get a better idea of the original buildings, stand back and look at the rooflines and upper floors.

Begin your historic walking tour at B Street and First Avenue.

Traveling south on B Street you will experience many styles of architecture dating back from the City’s incorporation in 1894 to the 1930s.

As you approach Third Avenue from B Street, your tour continues westward on Third Avenue to El Camino Real.

Once reaching El Camino, cross to the opposite side of Third Avenue and continue east back to B Street.

Continue north on B Street to Baldwin Avenue.

Head west on Baldwin Avenue to Ellsworth Avenue, then continue traveling to the south.

From Ellsworth Avenue turn left onto Second Avenue. Travel east to B Street, where the tour ends.

Enjoyed your historic walking tour of Downtown San Mateo, more details are here. Stay awhile and experience the lovely parks, shopping and restaurants in modern day San Mateo.

Public transportation information and more options to move around or tour the area.

County and branch library information, hours, and activities.

Reserve park areas, dog park rules, sports facility locations, pool information and more.